Caper in the Castro [MAC] Cathleen M. Ralph / Heizer Software 1989

This is considered to be the first video game with an LGBT theme. The game was thought to be lost in 21st century until 2017 when the author found original floppies of it. When Tessy LaFemme goes missing, her friend Tracker McDyke must put her detective skills to use and scour The Castro in San Francisco to track her down. This graphic adventure mystery game puts the player in the role of the detective. Its gameplay is presented through a mix of a point-and-click interface and a text parser. The player can click on items in the main game screen to interact with them. Verb icons give the player extra ways to interact, and some of these require the player to type what they want to do. An edited version was released under the title Murder on Main Street due to concerns a publisher would refuse to accept an LGBT-themed game. This version was released for free as charityware; the author requested that players donate to AIDS charities if they enjoyed the game. An alternative version of the game called Murder on Mainstreet was made for commercial sale. This version swapped out the main characters' names and other details to exclude LGBT themes, so that the developer could sell it to a publisher that might not have been interested in an LGBT-related game.
Browser-Playable Full Demo (uploaded by Internet Archive Software Collection)
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Murder on Mainstreet - Browser-Playable Full Demo (uploaded by Internet Archive Software Collection)
MAC Full Demo 914kb (uploaded by Macintosh Garden)

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